ChemCatChem

Cover image for Vol. 2 Issue 5

May 10, 2010

Volume 2, Issue 5

Pages 473–575

  1. Cover Picture

    1. Top of page
    2. Cover Picture
    3. Graphical Abstract
    4. News
    5. Minireviews
    6. Highlights
    7. Communications
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    1. Cover Picture: The Catalytic Conversion of Thiophenes over Large H-ZSM-5 Crystals: An X-Ray, UV/Vis, and Fluorescence Microspectroscopic Study (ChemCatChem 5/2010) (page 473)

      Marianne H. F. Kox, Ana Mijovilovich, Jesper J. H. B. Sättler, Eli Stavitski and Bert M. Weckhuysen

      Version of Record online: 30 APR 2010 | DOI: 10.1002/cctc.201090018

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      The cover picture shows an individual zeolite H-ZSM-5 crystal, the interior of which acts as a black box during the catalytic conversion of thiophenes. In their paper on page 564 ff., Weckhuysen et al. demonstrate how, with the combined use of X-ray absorption, UV/Vis and confocal fluorescence microspectroscopy, the black box can be opened to provide chemical images of individual H-ZSM-5 zeolite crystals. Additionally, the approach provides information on the formation, alignment, and distribution of reaction products.

  2. Graphical Abstract

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    2. Cover Picture
    3. Graphical Abstract
    4. News
    5. Minireviews
    6. Highlights
    7. Communications
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  3. News

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    3. Graphical Abstract
    4. News
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  4. Minireviews

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    1. You have free access to this content
      Minimal Hydrolases: Organocatalytic Ring-Opening Polymerizations Catalyzed by Naturally Occurring Carboxylic Acids. (pages 487–492)

      Pablo Domínguez de María

      Version of Record online: 15 APR 2010 | DOI: 10.1002/cctc.201000030

      Thumbnail image of graphical abstract

      It's only natural: Some naturally occurring carboxylic acids—in particular, α-hydroxycarboxylic acids—are useful catalysts for environmentally friendly ring-opening polymerizations and for (trans)esterifications, offering the advantageous selectivities of enzymes, but with a broader scope for reaction conditions more reminiscent of chemocatalysts. They are readily available on large scale by fermentative routes.

    2. Gold-Catalyzed Cross-Couplings: New Opportunities for C[BOND]C Bond Formation (pages 493–497)

      Pierre Garcia, Max Malacria, Corinne Aubert, Vincent Gandon and Louis Fensterbank

      Version of Record online: 18 MAR 2010 | DOI: 10.1002/cctc.200900319

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      From C to shining C: The fast-expanding field of gold catalysis has recently been extended to cross-couplings, including Suzuki and Sonogashira reactions. From the AuI/AuIII redox couple to the development of tandem routes, gold exhibits an impressive potential for cross-coupling reactions. The combination of gold with palladium gives rise to yet further synthetic opportunities.

  5. Highlights

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    1. Fullerene-Mediated Activation of Dihydrogen: A New Method of Metal-Free Catalytic Hydrogenation (pages 499–500)

      Jochen Niemeyer and Gerhard Erker

      Version of Record online: 8 APR 2010 | DOI: 10.1002/cctc.201000038

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      A new type of metal-free catalytic hydrogenation has been developed, which allows for the reduction of various nitroarenes to the corresponding anilines with excellent yields and chemoselectivities. The hydrogenation takes place under very mild conditions using dihydrogen in combination with fullerene catalysts.

      Corrected by:

      Corrigendum: Corrigendum: Fullerene-Mediated Activation of Dihydrogen: A New Method of Metal-Free Catalytic Hydrogenation

      Vol. 3, Issue 4, 629, Version of Record online: 5 APR 2011

    2. Copper-Catalyzed Asymmetric β-Boration of α,β-Unsaturated Carbonyl Derivatives (pages 501–504)

      Luca Mantilli and Clément Mazet

      Version of Record online: 15 FEB 2010 | DOI: 10.1002/cctc.201000008

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      The β generation: Transition metal- catalyzed asymmetric β-boration of α,β- unsaturated carbonyl derivatives has recently received much attention. Although a variety of metals can be used to promote this reaction, copper has recently emerged as the candidate of choice. Given the appropriate chiral ligand and reaction conditions, the challenging β-boration of β,β-disubstituted cyclic enones is achieved with excellent yields and enantioselectivities.

  6. Communications

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    1. (S)-Indoline-3-Carboxylic Acid: A New Organocatalyst for the Anti Mannich-Type Reaction (pages 505–508)

      Jörg Pietruszka and Robert Christian Simon

      Version of Record online: 8 APR 2010 | DOI: 10.1002/cctc.201000041

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      Enantiopure indoline-3-carboxylic acid is synthesized using an enzymatic kinetic resolution as a key step (E≫100). It is applied as an organocatalyst in Mannich-type reactions, which proceed with high anti selectivity at low temperatures, affording the products in moderate to good yields and in excellent enantiomeric excess.

    2. Convenient Carbonylation of Aryl Bromides with Phenols to Form Aryl Esters by Applying a Palladium/Di-1-adamantyl-n-butylphosphine Catalyst (pages 509–513)

      Xiao-Feng Wu, Helfried Neumann and Matthias Beller

      Version of Record online: 9 APR 2010 | DOI: 10.1002/cctc.201000016

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      Ester-day once more: Palladium-catalyzed carbonylation of aryl and heteroaryl bromides with phenols proceeds smoothly in the presence of di-1-adamantyl-n-butylphosphine (cataCXium® A). Twenty different aryl esters with a wide variety of substituents, are obtained in good to excellent yields under mild reaction conditions (0.1–0.2 MPa CO, 1 mol % Pd(OAc)2).

    3. Autoreduction and Catalytic Performance of a Cobalt Fischer–Tropsch Synthesis Catalyst Supported on Nitrogen-Doped Carbon Spheres (pages 514–518)

      Haifeng Xiong, Mahluli Moyo, Matthew K. Rayner, Linda L. Jewell, David G. Billing and Neil J. Coville

      Version of Record online: 18 MAR 2010 | DOI: 10.1002/cctc.200900309

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      Cobalt oxide supported on N-CSs (ca. 700 nm), prepared by deposition precipitation and autoreduced by the carbon supports, gives good performance as a catalyst for Fischer–Tropsch synthesis, better than that achieved by similar catalysts reduced with hydrogen. This effect is related to the trapping of the cobalt in cavities on the eroded carbon surface.

    4. One-Pot Synthesis of Bicyclic Fused Cyclopentenone Derivatives from 1-Ethynylcycloalkanols and Aldehydes (pages 519–522)

      Victorio Cadierno, José Gimeno and Noel Nebra

      Version of Record online: 16 APR 2010 | DOI: 10.1002/cctc.200900269

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      Give ′em enough Rupe: A straightforward route to bicyclic fused cyclopentenone derivatives, involving a Rupe rearrangement/aldol condensation/Nazarov cyclization sequence, has been developed starting from readily available 1-ethynylcycloalkanols and aldehydes in the presence of the 16- electron allyl-ruthenium(II) precatalyst [Ru(η3-2-C3H4Me)(CO)(dppf)][SbF6] and trifluoroacetic acid.

    5. Coupling of Alcohols over Alkali-Promoted Cobalt–Molybdenum Sulfide (pages 523–526)

      Jakob M. Christensen, Peter A. Jensen, Niels C. Schiødt and Anker D. Jensen

      Version of Record online: 9 APR 2010 | DOI: 10.1002/cctc.200900239

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      Double or nothing: Higher alcohols are produced by the hydrogenation of CO with a K-promoted Co–MoS2/C catalyst. Ethanol, which is passed over the sulfide catalyst along with CO and H2, is mainly converted into 1-butanol, which indicates that alcohol condensation contributes to the build-up of higher alcohols over the sulfide catalyst. In a nitrogen atmosphere, ethanol is also in part converted into 1-butanol, although ethyl acetate is the major product.

  7. Full Papers

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    1. Isotopic Oxygen Exchange over Pd/Al2O3 Catalyst: Study on C18O2 and 18O2 Exchange (pages 527–533)

      Satu Ojala, Nicolas Bion, Sérgio Rijo Gomes, Riitta L. Keiski and Daniel Duprez

      Version of Record online: 9 APR 2010 | DOI: 10.1002/cctc.201000033

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      Exchange would do you good: Labeled C18O2 was used to study oxygen isotopic exchange over Pd/Al2O3 catalyst. The improvement in exchange rate compared with the exchange from 18O2 is at least a factor of ten. The roles of PdO and carbonates are essential in enhancing the oxygen exchange from C18O2. C18O2 exchange can be applied instead of 18O2, when oxygen activation on Pd/Al2O3 catalysts is studied at low temperatures.

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      Highly Enantioselective Resolution of β-Amino Esters by Candida antarctica Lipase A Immobilized in Mesocellular Foam: Application to Dynamic Kinetic Resolution. (pages 534–538)

      Mozaffar Shakeri, Karin Engström, Anders G. Sandström and Jan-E. Bäckvall

      Version of Record online: 9 APR 2010 | DOI: 10.1002/cctc.201000027

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      Candida antarcticalipase A (CALA) immobilized in functionalized mesocellular foam (MCF) in the presence of sucrose facilitated a dramatic increase in enantioselectivity for the kinetic resolution (KR) of representative β-amino esters. The temperature of optimum activity of CALA shifted from 20–30 °C to 80–90 °C on immobilization in the MCF. Combination of the immobilized CALA with a ruthenium complex allowed dynamic KR at 90 °C.

    3. Formation of Furfural in Catalytic Transformation of Levoglucosan over Mesoporous Materials (pages 539–546)

      M. Käldström, N. Kumar, T. Heikkilä, M. Tiitta, T. Salmi and D. Yu. Murzin

      Version of Record online: 16 APR 2010 | DOI: 10.1002/cctc.201000024

      Thumbnail image of graphical abstract

      Catalytic transformation of levoglucosan (1-6-anhdyro-β-D-glucopyranose) and furfural is carried out in a fixed-bed reactor at 573 K over mesoporous material catalysts. Proton forms of MCM-41, MCM-48, SBA-15, and platinum form of MCM-48 catalysts are tested in the reaction, whereas H-Beta is used as a reference material. Oxygenated species are the main liquid products, consisting mainly of aldehydes and furfural.

      Corrected by:

      Corrigendum: Formation of Furfural in Catalytic Transformation of Levoglucosan over Mesoporous Materials

      Vol. 2, Issue 7, 717, Version of Record online: 7 JUL 2010

    4. Chemoselective Hydrogenolysis of Tetrahydropyran-2-methanol to 1,6-Hexanediol over Rhenium-Modified Carbon-Supported Rhodium Catalysts (pages 547–555)

      Kaiyou Chen, Shuichi Koso, Takeshi Kubota, Yoshinao Nakagawa and Keiichi Tomishige

      Version of Record online: 15 APR 2010 | DOI: 10.1002/cctc.201000018

      Thumbnail image of graphical abstract

      Modify M for diols: The industrially important monomer 1,6-hexanediol can be produced from hydrogenolysis of tetrahydropyran-2- methanol, which can be derived from acrolein or glycerol, using Re-modified Rh/C as a heterogeneous catalyst. Conventional catalysts such as M/C (M=Rh, Ru, Pd, or Pt), copper chromite and Raney nickel show poor activity and selectivity for this reaction.

    5. Support Effects in the Gold-Catalyzed Preferential Oxidation of CO (pages 556–563)

      Svetlana Ivanova, Véronique Pitchon, Corinne Petit and Valérie Caps

      Version of Record online: 8 APR 2010 | DOI: 10.1002/cctc.200900302

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      Preferential treatment: The promotion by hydrogen of gold-catalyzed, low temperature CO oxidation depends on the surface chemistry of the support used. It can be seen as a combination of gold reduction, the impact of water formation, from the reaction between O2 and H2, on the chemical composition of the catalyst surface, and the role of O2 and H2 in providing additional reaction pathways for CO elimination under preferential oxidation conditions.

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      The Catalytic Conversion of Thiophenes over Large H-ZSM-5 Crystals: An X-Ray, UV/Vis, and Fluorescence Microspectroscopic Study (pages 564–571)

      Marianne H. F. Kox, Ana Mijovilovich, Jesper J. H. B. Sättler, Eli Stavitski and Bert M. Weckhuysen

      Version of Record online: 16 APR 2010 | DOI: 10.1002/cctc.200900329

      Thumbnail image of graphical abstract

      Inner visions: Thiophene derivatives are chemically imaged during acid-catalyzed conversion within the micropores of individual coffin-shaped H-ZSM-5 zeolite crystals by X-ray absorption, UV/Vis, and confocal fluorescence microspectroscopy. A thiophene sulfur atom is found to be in a close proximity to two oxygen framework atoms and the reaction products are aligned within the straight pores of H-ZSM-5.

  8. Preview

    1. Top of page
    2. Cover Picture
    3. Graphical Abstract
    4. News
    5. Minireviews
    6. Highlights
    7. Communications
    8. Full Papers
    9. Preview
    1. You have free access to this content
      Preview: ChemCatChem 6/2010 (page 575)

      Version of Record online: 30 APR 2010 | DOI: 10.1002/cctc.201090021

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